I have two bachelor's degrees—one in Cinema Studies and one in Radio-Television, with a hands-on focus on broadcast technology. After college, I freelanced for production companies doing trade-show video and projection work, while also repairing phones and computers part-time.
After the pandemic, I moved into IT and spent about a year and a half providing white-glove support for a television studio. When industry strikes affected that role, I transferred within the account and spent another year and a half doing helpdesk and endpoint deployments. I then took a SysAdmin position at a consumer-products company, but I was laid off after only four months.
While unemployed, I completed several AWS classes through a community college, although I have not earned any certifications yet. I have also considered paying for a JAMF certification because I have substantial experience with Apple device management. My current job is a basic Tier 1 helpdesk contract covering someone's leave, and it ends later this year. I had hoped it would provide opportunities to grow, but the work is very limited.
I have applied to hundreds of jobs and interviewed for several, but I feel stuck. I no longer want to remain in helpdesk. Ideally, I would like to move toward backend infrastructure, cloud administration, automation, or another role where I can build things, work on challenging problems, and eventually earn over $100,000—preferably remotely. I live in a major West Coast city, so the local contract offers around $25 per hour are difficult to live on.
Should I pursue AWS, networking, security, or JAMF certifications? Would a degree program such as WGU help? How can I turn my current experience into a realistic path toward infrastructure or cloud work in this difficult job market?
3 Answers
A JAMF certification can be valuable if you specifically want Apple fleet-management or Mac administrator roles, but it will generally reinforce your endpoint-support profile rather than move you directly into cloud infrastructure. That is not necessarily bad, especially since you already have relevant experience, but make sure it matches the jobs you actually want.
An MSP could provide broader exposure to servers, identity, networking, Microsoft 365, backups, migrations, and different client environments. Those jobs can be demanding and sometimes have high turnover, so choose carefully, but the variety may help you escape being permanently assigned to basic tickets. Certifications are most useful when they support hands-on work and a clear target; they are much less effective as substitutes for experience.
You could also look at broadcast engineering, video-encoding infrastructure, or media-platform operations. Those roles may require more experience, but your production and IT background gives you a more credible starting point than someone coming from general helpdesk alone.
There is no guaranteed path into IT right now, and the market is rough even for people with many years of experience and several certifications. That does not mean your experience is worthless, but it does mean a remote job paying over $100,000 will be extremely competitive—especially if you restrict yourself to a particular city or entertainment-related employer.
Try broadening the industries you target. The same core tools can be used at a bank, manufacturer, law firm, university, or media company. Also define what you mean by “backend.” If you want cloud or infrastructure work, look for the skills that appear repeatedly in those job descriptions rather than collecting credentials at random. Linux, networking, scripting, Git, cloud platforms, automation, and infrastructure as code would likely be more useful than another general helpdesk credential.
That’s fair. My entertainment background is what gets me contacted most often, but I’m open to other industries. I’ve considered junior cloud roles, although I rarely see truly junior openings in my area.
I would not rush into a degree program or start buying certifications without first choosing a target role. Review several infrastructure, cloud administrator, or systems engineer postings and write down the common requirements you are missing. Then build a focused plan around those gaps.
For your goals, practical projects involving Linux, PowerShell or Python, AWS, networking, Git, monitoring, and Terraform could create a much stronger story. Document the projects in a small portfolio and describe the business problem, what you built, and how you tested it. Your four-month SysAdmin job still counts; a layoff does not erase the fact that you earned the position and performed the work.
Hundreds of applications with few results can also indicate a resume or targeting problem. Make separate versions for endpoint administration, systems administration, and cloud or infrastructure roles instead of presenting your entire background the same way every time. You are not starting from zero—you need to make your existing experience point clearly toward the next job.
This is probably the most useful advice I’ve received. I’ve been treating the short SysAdmin position like it barely counts, but I should present it as real experience and make the rest of my background tell a more consistent story.
I’ve noticed that pattern in my own career. I became good at L1 and L2 work but then got stuck there. My previous companies gave me MSP-style exposure inside larger organizations, though moving into the SysAdmin job turned out badly because of the employer rather than the work itself.